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Gas Chromatographic Analysis of Organic Acids in Japanese Green

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Gas Chromatographic Analysis of Organic Acids in Japanese Green Journal of Oleo Science Copyright ©2019 by Japan Oil Chemists’ Society doi : 10.5650/jos.ess19208 J. Oleo Sci. 68, (12) 1271-1277 (2019) Gas chromatographic Analysis of Organic Acids in Japanese Green Tea Leaves Nobuya Shirai＊ National Agriculture and Food Research Organization, Institute of Fruit Tree and Tea Science, 2769 Kanaya, Shimada, Shizuoka 428-8501, JAPAN Abstract: Herein, gas chromatography is used to determine and quantify organic acids in Japanese green tea leaves, and the established method is employed to profile the acid components of Matcha, Gyokuro, Sencha green teas, and green tea varieties and thus acquire data needed to ensure the high quality and safety of green tea. The tea leaves were esterified with 10 vol% sulfuric acid in 1-butanol at 100℃ for 2 h. Oxalic acid contents were high in Asatsuyu and Okuyutaka samples and were low in Sofu, increasing in the order of Sencha < Gyokuro < Matcha, while citric acid content increased in the order of Sencha < Matcha < Gyokuro. Moreover, the oxalic acid content of Gyokuro only slightly increased with increasing tea grade. The relative contents of the different fatty acids did not strongly vary between the different green tea varieties. However, the n-3 to n-6 ratio was found to be low in Sofu. The progressing maturity increased the n-3 to n-6 ratio of Yabukita. The n-3 to n-6 ratio was low in high-grade Matcha, Gyokuro, Sencha green teas, and was related to the green tea quality. The developed method was concluded to be suitable for the evaluation of green tea quality. Key words: fatty acid, gas chromatography, green tea, oxalic acid, organic acid 1 Introduction some studies, may increase the risk of kidney stone forma- Green tea enjoys global popularity and includes several tion6－10）. However, the intake of Sencha is not expected to varieties of tea. For example, Sencha green tea（hereafter induce kidney stone formation, as（i）this tea has a lower referred to simply as Sencha）is a popular and general oxalic acid content than Gyokuro and Matcha and（ii）epi- green tea in Japan. Gyokuro green tea（hereafter referred gallocatechin gallate contained in Sencha may actually to simply as Gyokuro）is a higher quality tea than Sencha, suppress kidney stone formation11, 12）. The growing export and requires more time to prepare than Sencha, including of Japanese green tea needs to be backed up by high tea a long shading period. Matcha green tea（hereinafter re- quality, and high oxalic acid content should therefore be ferred to simply as Matcha）is made by grinding Tencha avoided. Analysis of the organic acids in tea leaves is green tea, which is cultivated using more than 20 days of carried out via GC or capillary electrophoresis. Kamiya et shading. These green teas contain catechins and amino al. measured the oxialic acid content of green tea using acids, which are believed to benefit human health1, 2）. methyl esterification5）. However, this method is cumber- Moreover, high-grade green tea is characterized by a high some, and only oxalic acid can be measured. Capillary elec- content of amino acids, which, alongside with other com- trophoresis is not general equipment compared to GC or ponents, influence tea taste. Kaneko et al. reported that high performance liquid chromatography. Organic acid succinic acid and theogallin enhance the taste of glutamic analysis using GC-MS is often carried out via trimethylsi- acid in Matcha3）, while Horie et al. suggested that the taste lylation. Organic acids contain carboxyl groups; therefore, of green tea may be influenced by citric acid4）. However, these components can be easily analyzed using esterifica- succinic acid makes up a very low fraction of organic acids tion. However, the reported butanol method has a large in- found in green tea leaves4）, whereas the fraction of oxalic terday variation, and a stable value cannot be obtained13）. acid is usually high. Kamiya et al. indicated that high-grade In view of the above, one should clarify the organic acid Matcha is rich in oxalic acid, i.e., consumption of this tea contents of green tea to improve its quality. Herein, we leads to excessive oxalic acid intake5）, which, according to identify and quantify organic acids in Japanese green tea ＊Correspondence to: Nobuya Shirai, National Agriculture and Food Research Organization, Institute of Fruit Tree and Tea Science, 2769 Kanaya, Shimada, Shizuoka 428-8501, JAPAN E-mail: [email protected] Accepted September 20, 2019 (received for review August 21, 2019) Journal of Oleo Science ISSN 1345-8957 print / ISSN 1347-3352 online http://www.jstage.jst.go.jp/browse/jos/ http://mc.manusriptcentral.com/jjocs 1271 N. Shirai leaves（including commercial Matcha, Gyokuro, and 2.3 Esterication Sencha）using gas chromatography to ensure high tea Typically, a 15 mL screw cap test tube was sequentially quality and safety. charged with a 50 mg sample, 2,2-dimethoxypropane（20 μL）, 1-butanol（50 μL）containing glutaric acid as an inter- nal standard, and 10 vol％ sulfuric acid in 1-butanol（1 mL）, and heated at 100℃ for 2 h. During the reaction, the 2 Materials and Methods test tube was agitated every 15 min using a Vortex mixer. 2.1 Samples The test tube was cooled to room temperature, charged Crude tea leaves were collected in the field of the with n-hexane（3 mL）, and agitated again using the Vortex Kanaya Tea Research Station in April and May（2016 or mixer. Saturated sodium carbonate solution（1 mL）was 2018）. Matcha, Gyokuro, and Sencha tea leaves were pur- added, and the test tube was agitated again and left to chased（online or directly）in 2018. Gyokuro, and Sencha stand to allow the two phases to separate. The upper phase samples were powdered using a mill. was collected and transferred to another test tube, which was charged with distilled water（5 mL）, strongly shaken, 2.2 Chemicals and left to stand to achieve phase separation. The lower Sulfuric acid, 1-butanol, n-hexane, sodium carbonate, phase was discarded and washing with distilled water was 2,2-dimethoxypropane, oxalic acid, malic acid, succinic performed two more times. The wet organic phase was acid, and citric acid were purchased from Fujifilm Wako subjected to centrifugation, and the upper phase was col- Pure Chemical Corporation（Osaka, Japan）. Glutaric acid lected and analyzed by gas chromatography. was purchased from Tokyo Chemical Industry Co., Ltd. （Tokyo, Japan）. 2.4 Gas chromatographic analysis Organic acid analysis was performed on a gas chromato- Fig. 1 Chromatograms of Matcha（A）and rapeseed oil（B）. a: oxalic acid, b: succinic acid, c: malic acid, d: citric acid, I: palmitic acid, II: stearic acid, III: oleic acid, IV: linoleic acid, V: linolenic acid 1272 J. Oleo Sci. 68, (12) 1271-1277 (2019) Analysis of Organic Acids in Green Tea Leaves graph（GC-18A, Shimadzu Co., Ltd., Kyoto, Japan） equipped with a fused silica capillary column（Supelcowax 10; 30 m×0.25 mm i.d., Supelco Co., Ltd., Bellefonte, USA）and fitted with a CR6A integrator（Shimadzu Co., Ltd., Kyoto, Japan）. Helium was used as a carrier gas（flow rate＝1.4 mL/min）with a 25:1 split injection. The following temperature profile was employed: hold initial temperature of 100℃ for 2 min, heat to 170℃ at 10℃/min, then heat to 225℃ at 2.5℃/min, and perform isolation for 12 min. The injector and detector temperatures equaled 225 and 240℃, respectively. Organic and fatty acids were identified by comparison of their retention times with those of standard purified organic acids and rapeseed oil, respectively. Hy- droxyl group–containing malic and citric acids were quanti- fied using the relative response factors of the employed flame ionization detector14）. Esterification experiments were performed in triplicate for each sample, and the results were presented as means±standard deviations of three measurements. 3 Results and Discussion Organic and fatty acid butyl esters of Matcha and rape- seed oil were well separated（Fig. 1）. Figure 2 shows the changes of organic and fatty acid contents of Matcha with reaction time, revealing that malic, succinic, and citric acid contents were low during the first 30 min and stabilized after 60 min. The oxalic acid content was maximal after 120 min. The 16:0 percentage slightly increased, and the 18:3n-3 percentage decreased with increasing time. These changes of fatty acids might be due to oxidation with sulfu- ric acid. Therefore, 120 min was chosen as the optimal re- action time. The contents of oxalic, malic, succinic, and citric acids relative to that of glutaric acid（100％）equaled 107.2±1.2, 106.8±0.3, 58.1±0.5, and 73.8±2.4％, re- spectively. The recoveries of malic and citric acids were low, as these acids contain a hydroxyl group and 1-butanol was used as the reaction solvent. The slightly higher recov- ery of citric acid compared to that of malic acid was as- cribed to tributyl ester formation. These results imply that the established method may underestimate malic and citric acid contents. However, the developed method featured small relative standard deviations（oxalic acid: 2.1％, suc- Fig. 2 Organic acid contents and fatty acid profiles of cinic acid: 4.2％, malic acid: 2.4％, citric acid: 1.6％; see Matcha obtained for reaction times of 30, 60, 90, Fig. 2, 120 min）and was therefore sufficiently suited for and 120 min. comparative acid content analysis. A highly reproducible analytical value of for the organic acid in green tea was ob- acid content of tea leaves could not be measured using the tained because dimethoxypropane was substituted for an- developed method because of esterification ratio differenc- hydrous sodium sulfate.
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